To Sled or Not To Sled

Wondering how soon it's acceptable to wear a pair of Sleds to the office as a new analyst? Have previously only worn oxfords and brogues but want to change things up...
Also any recommendations for loafers that aren't Gucci Jordaan?


For context - An1 at mid-market IB (think Stifel, Houlihan, William Blair etc.)

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